Polymer based on a conjugated diene and a dienophilic component

ABSTRACT

Polymerization of a fatty acid or fatty acid derivatives containing conjugated double bonds and alkenes or alkynes containing electron acceptor substituents provides compositions useful as coatings, adhesives, sealants, fillers and the like.

BACKGROUND OF THE INVENTION

1. Field of the Invention

This invention relates to a polymer based on a conjugated diene anddienophilic component, to its production and to its use.

2. Discussion of Related Art

Such polymers are known. Thus, Japanese patent JA 93/1121 describes acopolymer produced from a maleic anhydride, a conjugated diene and analiphatic monoolefin. Butadiene was used as the conjugated diene andisobutene as the aliphatic monoolefin. The polymerization was carriedout in the presence of a peroxide at temperatures of around 150° C. Themolecular weight Mw is in the range from 500 to 50,000.

SUMMARY OF THE INVENTION

In Bull. Chem. Soc. Japan 40 (1967), pages 1272 to 1273, Iwamoto andYuguchi describe alternating copolymers of 2,4-hexadiene and maleicanhydride. The polymerization is initiated by heating and/or byradical-forming initiators. It may be carried out both in bulk and insolution. The yields are of the order of 2 to 97%.

Japanese patent JA 93/295041 also describes a copolymer of a conjugateddiene and maleic anhydride. Conjugated dienes are butadiene or isoprene.The catalyst used is an acetyl acetonate with metals of Group VII orGroup VIII. The polymer is used for coating, for surface treatment, forsealing and as an adhesive.

These known polymers have the following disadvantages:

DETAILED DESCRIPTION OF THE INVENTION

On the one hand, both monomers are based on petrochemicals and thus leadto a more negative ecological assessment by comparison with the use ofmonomers based on renewable raw materials. On the other hand, the rangeof raw materials for petrochemical conjugated dienes is limited tobutadiene and simple derivatives or homologs thereof. The use of theseshort-chain dienes represents not only a process-related disadvantage onaccount of the volatility and ready inflammability of these monomers.From the chemical perspective, too, these compounds only allow minorvariations in the chemical properties of the polymers. For example, noreactions with functionalized dienes are possible or indeed described.

Reaction products of maleic anhydride with fatty acids containingconjugated double bonds are also known. However, the reactions involvedhere are additions based on the Diels-Alder Reaction. This reaction isdescribed, for example, by Behr and Handwerk in Sci. Technol. 94 (1992),pages 206 to 208.

The problem addressed by the present invention was to provide newhigh-performance polymers based on renewable raw materials by aneconomic method.

The solution provided by the invention is defined in the claims and liesessentially in a polymer obtainable from:

A) at least one fatty acid with a conjugated C—C double bond orderivatives thereof,

B) at least one alkene or alkine component containing electron acceptorsubstituents and optionally

C) at least one copolymerizable alkene component with no electronacceptor substituents.

Component A

The “fatty acid containing a conjugated C—C double bond” (component A)is an aliphatic unsaturated carboxylic acid containing 6 to 32 and, moreparticularly, 16 to 24 carbon atoms which has two or more conjugated C—Cdouble bonds. This so-called conjuene fatty acid may be used infunctionalized form as an ester or amide for the polymerizationreaction.

One preferred embodiment of the invention is characterized by the use ofesters or partial esters of the conjuene fatty acids with monohydric orpolyhydric alcohols. “Alcohols” are understood to be hydroxylderivatives of aliphatic or alicyclic, saturated or unsaturated, linearor branched hydrocarbons. Both monohydric and dihydric alcohols orhigher alcohols may be used. Specific examples from the low molecularweight range include methanol, ethanol, propanol, butanol, pentanol,decanol, octadecanol, 2-ethylhexanol, 2-octanol, ethylene glycol,propylene glycol, trimethylene glycol, tetramethylene glycol,2,3-butylene glycol, hexamethylenediol, octamethylenediol, neopentylglycol, 1,4-bis-hydroxymethyl cyclohexane, Guerbet alcohol,2-methylpropane-1,3-diol, hexane-1,2,6-triol, glycerol, trimethylolpropane, trimethylol ethane, penta-erythritol, sorbitol, formitol,methyl glycoside, butylene glycol, reduced dimer and trimer fatty acidsand higher polyethylene, polypropylene and polybutylene glycols.Alcohols derived from colophony resins, such as abietyl alcohol, mayalso be used for the esterification. OH-containing tertiary amines mayalso be used.

Other suitable derivatives of the conjuene fatty acids are amides whichmay be obtained by reaction with ammonia, primary and secondary aminesor polyamines, for example with monoethanolamine, stearylamine,diethanolamine, ethylenediamine and hexamethylenediamine.

The “fatty acid containing a conjugated C—C double bond” may be obtainedin various ways.

The conjugated double bond may also have been originally present(naturally occurring conjuene fatty acids).

The conjugated double bond may be formed by selective hydrogenation offatty acids containing conjugated triple bonds (conjuene fatty acids byselective hydrogenation).

The conjugated double bond may also be formed by isomerization ofso-called isolene fatty acids either thermally or by the action ofcatalysts (conjuene fatty acids by isomerization). For example, theisolated double bonds in linoleic, linolenic, arachidonic andclupanodonic acid are converted into conjugated double bonds by theaction of catalysts. Specific isomerization catalysts are nickel onsupports, transition metals/noble metals, tert.butyl hypochloride,iodine/iodide, sulfur dioxide, selenium/selenium-containing catalysts,metal complexes, alkali metals, treated clays, sulfur-containingcatalysts, alkali metal alcoholates and alkali metal hydroxides.

In addition, the conjugated double bond may be formed by dehydration ofhydroxyfatty acids either from hydroxy compounds already containing acorrespondingly positioned double bond or from dihydroxyfatty acids. Thedehydration of hydroxyfatty compounds to conjugated fatty compounds islargely achieved by the addition of acidic catalysts.

Numerous catalysts are described in the literature, for example for thedehydration of castor oil, including for example hetero polyacids (U.S.Pat. No. 2,261,633, 1939), Na₂S₂O₇ (Paint Manuf. 19, 118, 1949),sulfuric acid (U.S. Pat. No. 2,392,119, 1946), phosphorous acid (GB671,368, 1952), boric acid (U.S. Pat. No. 2,278,425, 1939) and phthalicanhydride (U.S. Pat. No. 224,678), which lead to dehydrated castor oils.The conjugated fatty acids may be obtained from these oils byhydrolysis. However, acetylated hydroxyfatty compounds may be convertedinto the conjugated fatty acids by thermal ester pyrolysis. Thus,DE-C3-20 18 712, for example, describes the pyrolysis ofdiacetoxystearic acid methyl ester at 420 to 580° C. which is said togive conjuene yields of 80%.

Finally, the conjugated double bonds may be produced by partial or totalsyntheses.

The polymerization may have to be preceded by stereoisomerization intothe E,Z-, Z,E- or Z,Z-configuration.

The following are specific examples of fatty acids containing conjugateddouble bonds:

naturally occurring conjuene fatty acids, such as sorbic acid,2,4-decadienoic acid, 2,4-dodecadienoic acid, 10,12-octadecadienoicacid, 9-hydroxy-10,10-octadecadienoic acid,13-hydroxy-9,11-octadecadienoic acid,9,14-dihydroxy-10,12-octadecadienoic acid, 9,12,14-octadecatrienoicacid, 8,10,12-octadecatrienoic acid, elaeostearic acid (trichosanoicacid: punicic acid; catalpa acid), licanic acid, camolenic acid,parinaric acid;

conjuene fatty acids by selective hydrogenation, such as isanoic acid,isanolic acid, ximenynic acid, matricaria acid, lachnophyllic acid,mycomycinic acid;

conjuene fatty acids by isomerization of isolene fatty acids, forexample Edenor UKD 60/10(Henkel KGaA);

conjuene fatty acids by dehydration of hydroxyfatty acids, such asricinene fatty acid from ricinoleic acid.

Preferred components A are ricinene fatty acid, ricinene fatty acidmethyl ester, UKD fatty acids, UKD fatty acid methyl ester, dehydratedcastor oil, conjugated safflower oil and sunflower oil. The UKD fattyacids or fatty acid methyl esters are fatty acids and fatty acid methylesters with conjugated double bonds which can be obtained frompolyunsaturated fatty acids, more especially based on sunflower oil.

Component B1

An “alkene or alkyne component containing electronic acceptorsubstituents” (component B) is understood to be a compound containing 3to 100 and, more particularly, 4 to 32 carbon atoms which, adjacent theC—C double or C—C triple bond, contains at least one electron-attractingsubstituent, for example one of the following groups: —CN, —COOH, —CHO,—COR, —COOR, —CONH₂, —CONHR, —CONR² or —NO₂, where R is an alkyl groupcontaining 1 to 98 carbon atoms.

Specific examples are maleic acid, citric acid, itaconic acid, aconiticacid, acetylene dicarboxylic acid and 3,4,5,6-tetrahydrophthalic acid.However, derivatives of these acids, such as anhydrides, imides,alkylimides containing 1 to 30 carbon atoms in the alkyl group,nitriles, amides, alkyl and arylamides containing 1 to 30 carbon atomsin the alkyl/aryl group, aldehydes, esters and semiesters of alcoholscontaining 1 to 30 carbon atoms. Examples of such derivatives includemaleic anhydride, maleic imide, maleic acid dinitrile, maleic aciddihexyl ester, maleic acid benzyl butyl ester, fumaric acid dihexylester, fumaric acid dinitrile, fumaric acid monoethyl ester, itaconicanhydride, itaconic acid dimethyl ester, acetylene dicarboxylic aciddiethyl ester and 3,4,5,6-tetrahydrophthalic anhydride. Mixtures of thederivatives mentioned may also be used.

Preferred components B1 are maleic acid, citraconic acid, itaconic acid,aconitic acid, 3,4,5,6-tetrahydrophthalic acid and derivatives thereof.

Component B2

Besides the acids mentioned above, the corresponding derivatives of thefollowing acids may be used as a second component: crotonic acid,cinnamic acid, acrylic acid, methacrylic acid, cyanoacrylic acid and2,4-pentadienoic acid. These acids may also be used in the form ofderivatives, such as amides, alkyl and dialkyl amides containing 1 to 30carbon atoms in the alkyl group, nitriles, aldehydes, esters andsemiesters of alcohols containing 1 to 30 carbon atoms. Examplesinclude, methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl,sec.butyl and tert.butyl, n-pentyl, n-hexyl, 2-ethylhexyl, cyclohexyl,n-heptyl, n-octyl, phenylethyl, 2-methoxyethyl, 2-butoxyethyl,phenylpropyl and furfuryl acrylate and methacrylate; also cinnamic acidethyl ester, crotonic acid amide, methacrylamide, acrylamide, ethylcyanoacrylate, methyl crotonate, crotonic acid nitrile, cinnamic acidbenzyl ester and cinnamic aldehyde.

Component C

An “alkene with no electron acceptor substituents” (component C) is, forexample, a vinyl ether, vinyl ester, x-olefin, styrene derivative,conjugated hydrocarbon or vinyl pyrrolidone, the alkyl group of theethers and esters containing 1 to 30 carbon atoms. Examples includevinyl acetate, propionate, butyrate, laurate and stearate, ethyl vinylether, 1-decene and α-methyl styrene, β-methyl styrene, vinyl tolueneand tert.butyl styrene, chlorostyrene, butadiene and isoprene. Preferredcomponents C are vinyl ether, vinyl ester, styrene and vinylpyrrolidone.

The molar ratio between components A, B and C is in the range from 1:0.1to 10:0 to 10 and preferably in the range from 1:0.5 to 1.5:0.2 to 10.

The average molecular weight (weight average Mw) of the polymersaccording to the invention is above 5,000 and preferably above 10,000.Molecular weights of up to 1,700,000 g/mole were obtained. The molecularweights were determined by gel permeation chromatography (see Examples).

The properties of the polymers according to the invention depend uponthe educts and the reaction conditions and range from soft, extremelytacky through rubber-elastic to non-tacky, solid polymers.

Basically, the polymers according to the invention may be preparedsimply by mixing the reaction components A and B and optionally C andheating the resulting mixture.

The polymers according to the invention may be prepared both in bulk andin solution or dispersion. Suitable solvents are those which do not havea radical-inhibiting effect. The solvents used are selected, forexample, from ethers, such as tetrahydrofuran and dioxane; alcohols,such as methanol, ethanol and isopropanol; esters, such as ethylacetate, propyl acetate and n-butyl acetate; glycol ether acetates, suchas methyl, ethyl and butyl glycol acetate; ketones, such as acetone andcyclohexanone; dialkyl carboxylic acid amides, such as dimethylformamide, dimethyl acetamide and N-methyl pyrrolidone; aromatichydrocarbons, such as benzene, toluene and the xylenes; aliphatichydrocarbons, such as hexane and isooctane; alicyclic hydrocarbons, suchas cyclohexane; and chlorinated hydrocarbons, such as methylenechloride, chloroform, dichloroethane and tert.butyl chloride. Othersuitable solvents are substances which, by virtue of their low vaporpressure, are normally used as plasticizers, for example fatty acidesters, polyethylene glycols and phthalic acid esters.

However, the polymerization may also be carried out as emulsionpolymerization (droplet polymerization).

If no initiators are used, the reaction temperature should be in therange from 20 to 250° C. and more particularly in the range from 80 to200° C. Since the reaction is exothermic, it is sufficient to heat thereaction mixture to temperatures of 40 to 150° C. If radical-forminginitiators are used, temperatures of 0 to 200° C. and, moreparticularly, 30 to 150° C. are sufficient as the reaction temperature.

Suitable radical initiators are acetyl cyclohexane sulfonyl peroxide,peroxydicarbonates, diisopropyl peroxydicarbonate, t-amylperneodecanoate, t-butyl perneodecanoate, t-amyl perpivalate,bis-(2,4-dichlorobenzoyl)-peroxide, t-butyl perpivalate,bis-(3,5,5-trimethylhexanoyl) peroxide, dioctanoyl peroxide, didecanoylperoxide, dilauroyl peroxide, bis-(2-methylbenzoyl)-peroxide, succinylperoxide, diacetyl peroxide, dibenzoyl peroxide, t-butyl-per-2-ethylhexanoate, bis-(4-chlorobenzoyl)-peroxide, t-butyl perisobutyrate,t-butyl permaleate, 1,1-bis-(t-butylperoxy)-3,5,5-trimethyl cyclohexane,1,1-bis-(t-butylperoxy)-cyclohexane, t-butylperoxyisopropyl carbonate,t-butyl-per-3,5,5-trimethylhexanoate,2,5-dimethylhexane-2,5-diperbenzoate, t-butyl peracetate, t-amylperbenzoate, t-butyl perbenzoate, 2,2-bis-(t-butylperoxy)-butane,2,2-bis-(t-butylperoxy)-propane, dicumyl peroxide, t-butyl cumylperoxide, 3-t-butylperoxy-3-phenyl phthalide,bis-(t-butylperoxyisopropyl)-benzene, 2,5-dimethylhexane-2,5-di-t-butylperoxide, 3,5-bis-(t-butylperoxy)-3,5-dimethyl-1,2-dioxalane, di-t-butylperoxide, 2,5-dimethylhexine-3,2,5-di-t-butyl peroxide,3,3,6,6,9,9-hexamethyl-1,2,4,5-tetraoxacyclononane, p-menthanehydroperoxide, pinane hydroxide, diisopropylbenzene monohydroperoxide,cumene hydroperoxide, t-butyl hydroperoxide,azo-bis-(2,4-dimethylvaleronitrile), azo-bis-(isobutyronitrile), dibutylperoxydicarbonate, diisononanoyl peroxide, t-butyl perisononanoate,di-t-butyl peroxide, 1,1-bis-(t-butylperoxy)-3,5,5-trimethylcyclohexane, 3,5-bis-(t-butylperoxy)-3,5-dimethyl-1,2-dioxolane,2,5-dimethylhexine-2,5-di-t-butyl peroxide, acetyl cyclohexane sulfonylperoxide, dicyclohexyl peroxydicarbonate,bis-(4-t-butylcyclohexyl)-peroxydicarbonate, di-2-ethylhexylperoxydicarbonate, dimyristyl peroxydicarbonate, dicetylperoxydicarbonate, t-butyl perisononanoate, t-butyl perbenzoate, t-butylperpivalate, t-butyl peroxymaleate, t-butyl peroxybenzoate, dicumylperoxide, didecanoyl peroxide, methyl ethyl ketone peroxide,2,2′-azo-bis-(2,2-dimethylvaleronitrile),2,2′-azo-bis-(2,3-dimethylbutyronitrile) and2,2′-azo-bis-isobutyronitrile.

These radical initiators are used in quantities of 0.05 to 10% by weightand, more particularly, in quantities of 0.1 to 3% by weight, based oncomponent A.

It has surprisingly been found that, in the case of technical conjuenefatty acids containing saturated and unsaturated fatty acids, such asstearic, oleic and linoleic acid, as secondary components, thepolymerization reaction is not inhibited although the unsaturated fattyacids containing isolated double bonds do themselves have inhibitorproperties. Accordingly, the reaction product generally contains thesevery fatty acids or derivatives thereof as an extractable secondaryconstituent. The crude polymers therefore had soft-elastic propertieswhich can be advantageous for special applications. Plasticizer-freepolymers can be obtained by purification, for example by distillation orfractional precipitation.

Where polymerization is carried out in solution, the polymer canprecipitate. Should this not be the case, the polymer is precipitated byaddition of a solvent with a lower or higher polarity than the reactionmedium. In general, the monomeric secondary products remain in solutionwhere working up is carried out in this way and can thus be removed. Thepolymers can also be fractionated by dissolution and precipitation, forexample with acetone/hexane or acetone/water mixtures. The polymers mayalso be freed from monomers and other low molecular weight substances bydistillation.

The polymers thus produced may be directly used for coating, bonding,sealing, filling or as a material.

However, the reactive groups in the polymer may also be completely orpartly reacted. Carboxylic acid or derivatives thereof, above all theanhydride group of the polymer according to the invention, are suitablefor this purpose.

The polymer-modifying reagents may be monofunctional or polyfunctional.

The functionalities well known from organic chemistry may serve as thefunctional groups. These include, above all, hydroxy, mercapto, ether,ester, carboxyl, carboxylate, amino and amido groups. Groups reactive tothe polymer are, above all, epoxy, isocyanate, mercapto, hydroxy andamino groups. Specific examples of polymer-modifying reagents are

alcohols, such as methanol, ethanol, isopropanol, butanol, long-chainfatty alcohols, unsaturated fatty alcohols, branched fatty alcohols,fatty alcohol ethoxylates, abietol, benzyl alcohol, phenoxyethanol,monoethanolamine, diethanolamine, triethanol amine, ethylene glycol,propylene glycol, polyethylene glycols, polypropylene glycols,hexane-1,6-diol, 1,12-dihydroxyoctadecane, glycerol diacetate,1,2-O-isopropylidene glycerol, monoacyl glycerides, ricinoleic acidmethyl ester, lactic acid ethyl ester, hydroxybutyric acid;

amines, such as butylamine, octadecylamine, benzylamine,ethylenediamine, hexamethylenediamine, Jeffamines, 1,4-phenylenediamine;

epoxides, such as ethylene oxide, propylene oxide, cyclohexene oxide,α-olefin oxides, epoxidized fats and oils, epoxidized fatty acids andalkyl esters thereof, epoxy hardeners, such as bisphenol-A-diglycidylether.

The compounds obtained by the polymer-analog reaction may in turn befurther reacted, for example by oxidative post-curing in the presence ofsiccatives, grafting, dehydration to imides and reaction withisocyanates.

Salt formation, vulcanization, post-crosslinking with peroxides andhydrogenation are also mentioned as particular forms of polymermodification. So far as the reaction with salts is concerned, it isimportant to distinguish between monovalent and polyvalent metals. Thepolyvalent metals, for example calcium, zinc and aluminium, lead tocrosslinked polymers (ionomers), as described in DE 42 11 118.Crosslinked polymers may also be otherwise obtained where polyfunctionalreagents are used.

The polymer-analog reaction may be carried out in bulk or in solution.Only solvents which do not react with the functional groups of thepolymer are suitable, for example ethers, such as diethyl ether,tert.butyl methyl ether, tetrahydrofuran and dioxane; esters, such asethyl and propyl acetate and n-butyl acetate; glycol ether acetates,such as methyl, ethyl and butyl glycol acetate, ketones, such as acetoneand cyclohexanone; dialkyl carboxylic acid amides, such as dimethylformamide, dimethyl acetamide and N-methyl pyrrolidone; aromatichydrocarbons, such as benzene, toluene and the xylenes; aliphatichydrocarbons, such as hexane and isooctane; alicyclic hydrocarbons, suchas cyclohexane; and chlorinated hydrocarbons, such as methylenechloride, chloroform, dichloroethane and tert.butyl chloride.

However, the modifying reagent may also be used as the solvent. Forexample, alcohols, such as methanol, ethanol or isopropanol, and amines,such as butylamine, etc., may be used.

A plasticizer may also be used as the solvent in the modificationreaction.

The physical and chemical properties of the polymers according to theinvention initially formed may be significantly varied by thispolymer-analog reaction. Thus, a soft resin with extremely tackyproperties is obtained after treatment with methanol. The precipitationof polymers with solvents having a lower or higher polarity than thereaction medium leads to non-tacky elastic polymers which can be drawnto form transparent films.

The polymers according to the invention may be used for coating,bonding, sealing, filling and as a material, for example as hotmeltadhesives, tackifiers or high-tack dispersions. The polymers accordingto the invention in the form of their salts are also suitable asbuilders for detergents, as stabilizers for emulsions and as thickeners.

The polymers or modified polymers according to the invention may be usedin bulk, in solution or in emulsion/dispersion. By virtue of theirvariable properties, they may be used as binders, adhesives, adhesivesealing compounds and coatings. They are particularly suitable forsubstrates varying in their elastic behavior or in their thermalexpansion coefficient, as is generally the case with differentsubstrates. Suitable substrates are metals, such as aluminium, wood,paperboard, paper, wall coverings, such as wallpaper, cork, leather,felt, textiles, plastics (particularly floor coverings of PVC, linoleumand polyolefins), mineral substrates, such as glass, quartz, slags, rockand ceramics and metals. The plastics may be present in the form offilms, sheets or other molded products.

The polymers or modified polymers according to the invention areparticularly suitable for the production of printing ink binders,adhesive sticks, floor covering adhesives, multipurpose adhesives,plastisols, hotmelt adhesives or hotmelt sealants and paste-formsealants, such as jointing compounds. They may also be used for coatinghard surfaces, textiles and paper.

The polymers or modified polymers according to the invention areextrudable and are therefore suitable for injection molding. They may beused, for example, as materials.

The polymers or modified polymers according to the invention, moreparticularly the salts and reaction products with polyethylene glycols,are suitable as polymeric emulsifiers, dispersants, thickeners orbuilders for detergents.

The low molecular weight polymers or modified polymers are suitable assoft resins and as tackifiers for modifying other commercially availablepolymers and polymer dispersions.

The invention is illustrated by the following Examples.

EXAMPLES

A) Test Methods

1) The glass transition temperature (TG) was determined as follows: DSC910 measuring cell with DuPont 2100, Al crucible with 5 holes in itslid, 3 l/h N₂, 20 K/min.

2) The molecular weights were determined by gel permeationchromatography (GPC) carried out as follows:

mobile solvent: tetrahydrofuran p.a.

column system: Waters Styragel column set (6 in-tandem columns with 106,105, 104, 103, 500 and 100 Angstroems, each measuring 300×7.8 mm)

throughflow: 1.0 ml/min.

detection: RID 6A RI detector (Shimadzu)

detector range: 128

chromatography

data system: Spektra data system

duration: 75-90 mins.

sample preparation: about 100 to 200 mg of sample are carefully weighedinto 50 ml measuring flasks and made up to the mark with THF. Afterwaiting for at least 8 hours, aliquots of the sample solutions arefiltered through a filter attachment and then chromatographed.

calibration: polystyrene with various molecular weights disolved solvedin THF (a product of PSS)

The number averages (Mn) and weight averages (Mw) of the molecularweights are shown.

3) The tensile shear strengths were determined as follows:

test specimen: beech plywood, rigid PVC, aluminium size: 25×80 mm²bonded area: 25×20 mm²

storage: standard conditioning atmosphere of 23° C./50% relativehumidity incubator, 40°+0.5° C.

testing machine: Instron Series 4200

Test Parameters

speed 50 mm/minute

force transducer 10 KN (max.)

control PC, Instron 104 Materials Testing System

number of test specimens 5 per sample

4) The oleochemical characteristics were determined by the following DGFmethods:

acid value (AV): DGF C-V 2

saponification value (SV): DGF M-IV 2

hydroxyl value (OHV): DGF C-V 17b

iodine value (IV): DGF C-V 11d

The acid value (AV), saponification value (SV) and hydroxyl value (OHV)are shown in mg KOH/g while the iodine value (IV) is shown in giodine/100 g.

B) The following raw materials were used:

1) Conjuene fatty acid Edenor UKD 60/10 (a product of Henkel KGBA) withthe following specification:

AV: 198-203

IV: 138-148

percentage of conjugated fatty acids: 56-67%

linoleic acid: 2-9%

oleic acid: 19-34%

2) Ricinene fatty acid Dedico 5981 (a product of Unichema) with thefollowing specification:

AV: 193-198

SV: 195-202

C) Examples

Example 1

Reaction of Ricinene Fatty Acid with Maleic Anhydride

900 g of ricinene fatty acid and 196.9 g of maleic anhydride wereweighed into a 2 liter three-necked round-bottomed flask. Astirrer-equipped apparatus with two reflux condensers placed one abovethe other was used as the reactor. The lower reflux condenser wasconnected to a thermostat set to 55° C. to ensure that the maleicanhydride did not crystallize in the condenser. The upper refluxcondenser was cooled with tap water. The reactor was slowly heated witha heating mushroom. At an internal temperature of 50° C., the maleicanhydride melted and the exothermic reaction began. After the heateffect had abated, the reaction mixture was heated to 115° C. Theviscosity of the yellow-orange clear liquid increased over a period of30 minutes. The heat was then removed. At room temperature, the productwas yellow, clear and highly viscous.

According to GPC, the product consisted of two fractions. The lowmolecular weight fraction of 51.7% had a molecular weight Mn of 392dalton and Mw of 485 dalton. The high molecular weight fraction of 48.3%had a molecular weight Mn of 15991 dalton and Mw of 40402 dalton.

Example 2

a) Production of Ricinene Fatty Acid Methyl Ester

2,000 g of ricinene fatty acid, 2,193 g of methanol and 19.2 g ofmethane sulfonic acid were weighed into a stirred apparatus with a 6liter three-necked round-bottomed flask. The reactor was heated to 67°C. with a heating mushroom and boiled under reflux. The initially clearyellow liquid became more cloudy during the reaction. After about 8 h,the acid value was 5 and the reaction was terminated. The excessmethanol/H₂O was distilled off in vacuo (˜10 mbar) up to 75° C. Theproduct was then washed with hot water until neutral and was then dried.The methyl ester was distilled in a high vacuum up to a bottomtemperature of 180° C. 10% was taken as first runnings. After cooling,the product was yellow, clear and liquid.

Characteristic data:

AV: 5.2

OHV: 3

V: 192

GPC: Mn=283 dalton, Mw 334 dalton

b) Reaction of Ricinene Fatty Acid Methyl Ester with Maleic Anhydride

600 g of ricinene fatty acid methyl ester and 132 g of maleic anhydridewere introduced into a 2 liter three-necked round-bottomed flask. Astirred apparatus with two condensers (see Example 1) was used as thereactor while a heating mushroom was used as the heat source. Thecontents of the reactor were then heated to 110° C. and boiled for 6 h.The reaction was then terminated. The product was yellow, clear andslightly viscous at room temperature. According to GPC, the productconsisted of two fractions. The low molecular weight fraction of 46.6%had a molecular weight Mn of 364 dalton and Mw of 431 dalton. The highmolecular weight fraction of 53.4% had a molecular weight Mn of 11905dalton and Mw of 32864 dalton.

c) Partial Distillation of the Ricinene Fatty Acid Methyl Ester/MAPolymer

300 g of the reaction product of ricinene fatty acid methyl ester withmaleic anhydride (Example 2a) were heated with a heating mushroom in a500 ml two-necked round-bottomed flask. The contents of the flask wereheated with stirring (magnetic stirrer) in a high vacuum to a bottomtemperature of 240° C. and distilled. The residue (202.2 g) was anextremely tacky resin; the distillate (97.8 g) was light yellow andliquid. According to GPC, the product consisted of two fractions. Thelow molecular weight fraction of 26.1% had a molecular weight Mn of 462dalton and Mw of 517 dalton. The high molecular weight fraction of 73.9%had a molecular weight Mn of 9174 dalton and Mw of 28957 dalton.

Example 3

Reaction of Edenor UKD 60/10 with Maleic Anhydride

800 g of Edenor UKD 60/10 and 192 g of maleic anhydride were weighedinto a stirred apparatus comprising a 2 liter three-neckedround-bottomed flask. The reaction began exothermically on gradualheating, the temperature rising beyond 100° C. A yellow rubber-elasticmaterial was obtained after cooling to room temperature. According toGPC, the product consisted of 2 fractions. The low molecular weightfraction of 35% had a molecular weight Mn of 345 dalton and Mw of 428dalton. The high molecular weight fraction of 65% had a molecular weightMn of 9191 dalton and Mw of 36486 dalton.

Example 4

a) Preparation of Edenor UKD 60/10 methyl ester

For esterification, 1,820 g of Edenor UKD 60/10, 2,080 g of methanol and15.6 g of methane sulfonic acid were introduced into a 6 literthree-necked round-bottomed flask and nitrogen was passed over. After 5h at 67° C. (reflux), the product had an acid value of 4. At 80° C., amixture of methanol/H₂O was distilled off in vacuo (ca. 10 mbar). Theproduct was then washed with hot water until neutral and wassubsequently dried. First runnings of 5% were taken in a high vacuum,followed by distillation up to a bottom temperature of 180° C. Thedistilled methyl ester was yellow, clear and liquid.

AV: 6.7

SV: 201

OHV: 2.3

GPC: Mn=304 dalton and Mw=358 dalton

b) Reaction of Edenor UKD 60/10 methyl ester with maleic anhydride 1,325g of Edenor UKD 60/10 methyl ester and 26.5 g of maleic anhydride wereweighed into a 4 liter three-necked round-bottomed flask equipped with astirrer and boiled for 7 h at 116° C. After cooling, the product wasyellow, clear and viscous. According to GPC, the product consisted of 2fractions: the low molecular weight fraction of 48% had a molecularweight Mn of 269 dalton and Mw of 383 dalton. The high molecular weightfraction of 52% had a molecular weight Mn of 12266 dalton and Mw of43936 dalton.

c) Distillation of Edenor UKD 60/10 Methyl Ester/MA Polymer

200 g of the reaction product of Edenor UKD 60/10 with maleic anhydride(Example 4b) were heated with a heating mushroom in a 500 ml two-neckedround-bottomed flask. The contents of the flask were then heated withstirring (magnetic stirrer) in a high vacuum to a bottom ure of 240° C.and distilled. The residue (138.7 g) was yellow and tacky; thedistillate (71.3 g) was light yellow and liquid.

According to GPC, the product consisted of 2 fractions. The lowmolecular weight fraction of 21% had a molecular weight Mn of 273 daltonand Mw of 386 dalton. The high molecular weight fraction of 79% had amolecular weight Mn of 11355 dalton and Mw of 45113 dalton.

Example 5

a) Steam Treatment of the Edenor UKD 60/10/MA Polymer

500 g of Edenor UKD 60/10 and 120 g of maleic anhydride were weighedinto a 2 liter four-necked round-bottomed flask. The reaction took placeas in Example 3. After termination of the reaction, the apparatus wasaugmented by a steam inlet tube and a distillation bridge with adescending condenser. Steam was then introduced for 3 h at 100° C. Theproduct was white and creamy. After a while, water separated off.

b) Saponification of the Edenor UKD 60/10/Ma Polymer with KOH

100 g of the reaction product of Edenor UKD 60/10MA with maleicanhydride (see Example 3) were introduced into a 500 ml three-neckedround-bottomed flask. 64 g of potassium hydroxide (50%) and 98.3 g ofwater were added dropwise, followed by stirring for 3.5 h at 80° C.After cooling, the product was brown and viscous.

c) Saponification of the Edenor UKD 60/10/MA Polymer with Ammonia

100 g of the reaction product of Edenor UKD 60/10 with maleic anhydride(see Example 3) were dissolved in 400 g of acetone and 100 g of waterwere added to the resulting solution. The solution was concentratedwhile heating to around 200 ml under normal pressure. After cooling, awhite w/o emulsion was obtained. The emulsion did not wet glass. Afterstorage for 3 days, the color of the emulsion changed to beige.

5 g of Rilanit HRE 60 were added while heating to this emulsion andammonia was introduced with vigorous stirring until a pH value of 7 wasreached. After cooling, a clear, brown and highly viscous solution wasobtained. The solution is extremely stringy and dries to form an elasticfilm. The film turns very brittle in 3 to 4 weeks. The solution wassuitable for the bonding of paper. The setting time was 2 to 3 minutes.No greasy patches were observed.

Example 6 Reaction of Edenor UKD 60/10 with Maleic Anhydride in thePresence of Radical Initiators

58.8 g of maleic anhydride and 280.0 g of Edenor UKD 60/10 weredissolved in 200 ml of acetone and a solution of 2.2 g of dilauroylperoxide in 20 ml of acetone was added to the resulting solution. Thesolution was then slowly heated with stirring to 64° C. and refluxed forabout 8 hours. After cooling, half the highly viscous solution wasconcentrated by evaporation in vacuo. An extremely tacky and softpolymer film is obtained.

According to GPC, the product consisted of 2 fractions. The lowmolecular weight fraction of 40% had a molecular weight Mn of 333 daltonand Mw of 406 dalton. The high molecular weight fraction of 60% had amolecular weight Mn of 26551 dalton and Mw of 81231 dalton.

The polymer formed was precipitated from the other half of the reactionsolution by stirring in about 250 g of n-hexane. The solvents werelargely separated from the polymer by decantation, after which thepolymer was rewashed with n-hexane and the residual solvent was removedby distillation. An almost colorless, transparent and tack-free polymerwas obtained in a yield of 110 g. The polymer was readily soluble inacetone, tetrahydrofuran and methanol.

According to GPC, the product consisted of 2 fractions; the lowmolecular weight fraction of 12% had a molecular weight Mn of 344 daltonand Mw of 413 dalton. The high molecular weight fraction of 88% had amolecular weight Mn of 27471 dalton and Mw of 83444 dalton. Meltingrange: >150° C. after storage for 3 weeks TG: ca. 10° C. (after storagefor 2 weeks)

Example 7 Reaction of Edenor UKD 60/10 Methyl Ester with MaleicAnhydride in the Presence of Radical Initiators

58.8 g of maleic anhydride and 294 g of Edenor UKD 60/10 methyl ester(Example 4) were dissolved in 200 ml of acetone and a solution of 2.3 gof dilauroyl peroxide (DLP) in 20 ml of acetone was added to theresulting solution. The solution was then slowly heated with stirring to64° C. and refluxed for about 7 hours. After cooling, the reactionsolution was concentrated by evaporation in vacuo. A highly viscousgolden yellow liquid was obtained and was stirred with about 800 g ofn-hexane at room temperature. A white, extremely stringy deposit wasformed. Removal of the solvent by decantation and drying of the residuein vacuo left 210 g of a golden yellow, soft and elastic polymer.

According to GPC, the product consisted of 2 fractions; the lowmolecular weight fraction of 10% had a molecular weight Mn of 371 daltonand Mw of 446 dalton. The high molecular weight fraction of 90% had amolecular weight Mn of 24321 dalton and Mw of 79116 dalton. Meltingrange: 85-95° C. TG:−22 to −32° C.

Example 8 Reaction of Edenor UKD 60/10 Methyl Ester with MaleicAnhydride (MA) and Vinyl Acetate in the Presence of Radical Initiators

280 g of Edenor UKD 60/10, 58.8 g of MA, 51.6 g of vinyl acetate and 2.7g of DLP were dissolved in 200 g of acetone without heating at roomtemperature and the clear solution obtained was subsequently boiledunder reflux for 7.5 hours at around 70° C. After 2 hours, an increasein viscosity was discernible. The reflux temperature fell backcontinuously to 65° C. until the reaction was terminated. The next day,110 g of acetone were distilled off and the distillation residue waspurified, i.e. the low molecular weight fractions were extracted twicewith about 500 g of hexane. Removal of the solvent by decantation anddrying of the residue in vacuo left a clear, colorless, non-tackynon-elastic polymer.

According to GPC, the product consisted of 2 fractions. The lowmolecular weight fraction of 10% had a molecular weight Mn of 371 daltonand Mw of 446 dalton. The high molecular weight fraction of 86% had amolecular weight Mn of 64231 dalton and Mw of 1698000 dalton. TG:+23° C.

Example 9 Reaction of Edenor UKD 60/10 Methyl Ester with MaleicAnhydride and Acrylic Acid in the Presence of Radical Initiators

280 g of Edenor UKD 60/10, 58.8 g of MA, 43.2 g of acrylic acid and 2.7g of dilauroyl peroxide were dissolved in 200 g of acetone withoutheating at room temperature and the clear solution obtained wassubsequently boiled under reflux for 7.5 hours at around 71° C. After 2hours, an increase in viscosity is discernible. The reflux temperaturefell back continuously to 67° C. until the reaction was terminated. Thenext day, 114 g of acetone were distilled off and the distillationresidue was purified, i.e. the low molecular weight fractions wereextracted twice with 500 g of hexane. Removal of the solvent bydecantation and drying of the residue in vacuo left a clear, colorless,non-tacky and non-elastic polymer.

According to GPC, the product consisted of two fractions. The lowmolecular weight fraction of 10% had a molecular weight Mw of 511dalton. The high molecular weight fraction of 90% had a molecular weightMn of 47048 dalton and Mw of 142730 dalton. TG:+16° C.

Example 10 Purification of an Edenor UKD 60/10/MA Polymer

To prepare a particularly pure polymer, 601 g of Edenor UKD 60/10, 127 gof MA and 7.1 g of dilauroyl peroxide were reacted in methyl ethylketone/petroleum ether (472 g and 728 g) as in Example 6. Forpurification, the polymer initially precipitating was washed with 300 gof petroleum ether, taken up in 200 g of methyl ethyl ketone andprecipitated with 600 g of petroleum ether. The polymer was thenrewashed with 400 g of petroleum ether and dried. The product wascolorless and solid (GPC: 92% polymer). For further purification, thepolymer was redissolved in methyl ethyl ketone, precipitated withpetroleum ether and washed 4 times with 300 g of petroleum ether. Theproduct was colorless and solid (GPC: 98.6%) polymer with Mn=40,000 andMw=95,000).

Example 11 Hydrogenation of an Edenor UKD 60/10/MA Polymer

A polymer was prepared as in Example 6 from 650 g of Edenor UKD 60/10,137 g of MA and 7.9 g of dilauroyl peroxide in methyl ethylketone/petroleum ether (516 g and 787 g). The polymer was purified bywashing with 300 g of petroleum ether (GPC: 89% polymer with Mn=41,000).300 g of THF and 1.25 g of palladium on carbon were added to 100 g of a50% solution of this product in THF, followed by hydrogenation for 6hours at 80° C. under a hydrogen pressure of 100 bar. The product wasfiltered through Celite, the solvent was evaporated and the product wasthen dried. The product was colorless and brittle. The GPC shows a broadsignal at Mn=500,000 and Mw >10 million with a fraction of 85%.

Example 12 Reaction of an Edenor UKD 60/10/MA Polymer with Oleyl Alcohol

200 g of a 50% solution of a reaction product—similar to Example 6—of650 g of Edenor UKD 60/10 and 137 g of MA were reacted while stirringwith 15.8 g of dilauroyl peroxide in methyl ethyl ketone/petroleum ether(516 g and 787 g) and purified by washing with 300 g of petroleum ether.GPC: 82% polymer with Mn=42,000. The product was reacted with 72.5 g ofoleyl alcohol (Ocenol 90/95, Henkel KGaA) in THF for 3 hours at 70° C.After evaporation of the THF, 110 g of water and 16 g of 50% sodiumhydroxide were added, followed by stirring for 1 hour at roomtemperature. The resulting, approximately 50% solution is clear andhighly viscous.

Example 13 Reaction of an Edenor UKD 60/10/MA Polymer with EthyleneGlycol

0.6 g of ethylene glycol were refluxed with stirring for 4 hours in THFwith 50 g of a 15% solution of a reaction product similar to Example 6(650 g of Edenor UKD 60/10 and 137 g of MA with 15.8 g of dilauroylperoxide in methyl ethyl ketone/petroleum ether (516 g and 787 g),purification by washing with 300 g of petroleum ether, GPC: 82% polymerwith Mn=42,000). A clear colorless solution was formed. The solution wasconverted into a film on a Teflon plate. The film was clear, colorlessand hard. The GPC shows one signal at Mn=32,600 making up 89% and twosignals with peaks below 1,000 making up a total of 11%.

Example 14 Reaction of an Edenor UKD 60/10/MA Polymer with PolyethyleneGlycol

11.9 g of polyethylene glycol 600 dissolved in the same quantity of THFwere heated with stirring for 1 hour to 64° C. with 50 g of a 10%solution of a reaction product similar to Example 6 (650 g of Edenor UKD60/10 and 137 g of MA with 15.8 g of dilauroyl peroxide in methyl ethylketone/petroleum ether (516 g and 787 g), purification by washing with300 g of petroleum ether; GPC: 82% polymer with Mn=42,000) in THF and0.56 g of N-methyl imidazole. A yellow cloudy solution was formed. Aftercooling, the solidified solution turned into a gel which could easily bevibrated.

Example 15 Reaction of an Edenor UKD 60/10/MA Polymer with MagnesiumOxide

38.0 g of a 50% solution of a reaction product similar to Example 6 (650g of Edenor UKD 60/10 and 137 g of MA with 15.8 g of dilauroyl peroxidein methyl ethyl ketone/petroleum ether (516 g and 787 g), purificationby washing with 300 g of petroleum ether; GPC: 82% polymer withMn=42,000) in THF were intensively stirred with 2.0 g of magnesiumoxide. The mixture was dried in vacuo for 2 hours at 75° C. and formed alight yellow compound which was hard at room temperature but becameelastic on heating.

Example 16 Complete Esterification of an Edenor UKD 60/1 0/MA Polymer

A conjudiene fatty acid/MA polymer similar to Example 6 was reacted withexcess methanol in the absence of a catalyst to form the semiester(AV=145 mg KOH/g). 26.15 g of this methyl semiester polymer weredissolved in 200 g of dimethyl formamide and 19.2 g of methyl iodidewere added to the resulting solution with stirring. After 15 minutes,79.2 g of a 25% tetrabutyl ammonium hydroxide solution in methanol wereslowly added dropwise in 45 minutes to the solution which had changedcolor from pale yellow to golden yellow. After 10 to 15 minutes, theoriginally clear solution became cloudy. The solvents were distilledoff, the residue was taken up in 200 ml of tetrahydrofuran (THF) and theTHF-insoluble fraction was separated off. After about 700 ml of methanolhad been added to the clear filtrate, the polymer precipitated and thesupernatant solution was decanted off. The residual solvents were thenremoved from the polymer obtained by vacuum distillation. A lightyellow, soft, highly elastic and tacky polymer which no longer containedany low molecular weight components was obtained. Molecular weight(GPC): MW 93,000 AV: 4.6 mg KOH/g

Example 17 Reaction of an Edenor UKD 60/10/MA Polymer with Butylamine toform a Butylimide

a) Production of the Semi-Amide

300.1 g of the polymer of Example 6 were dissolved in about 500 g oftetrahydrofuran. A solution of 55.0 g of n-butylamine in about 60 g oftetrahydrofuran was then slowly added dropwise with stirring. After theaddition, the solution was refluxed for 2 hours and the solvent was thendistilled off. Yield: 355.2 polymer

Appearance of the polymer (semi-amide): yellow-brown, non-elastic,non-tacky

AV: 252 mg KOH/g (theor. 249)

b) Reaction of the semi-amide to form the imide

200 g of the butylamide were mixed with about 200 g of cumene and themixture was heated to its boiling temperature (about 155° C.) andrefluxed for 3.5 hours on a water separator. The cumene was thendistilled off. The amount of water removed came to 7.4 ml. According toGPC, the product consisted of 2 fractions. The conjudiene fatty acidN-butyl maleic imide polymer obtained is golden yellow, highly elasticand tacky. The low molecular weight fraction of 22% had a molecularweight Mw of 508 dalton. The high molecular weight fraction of 78% had amolecular weight Mn of 52602 dalton and Mw of 153855 dalton.

AV: 140 mg KOH/g (theor. 130)

Example 18 Bonding Tests with a 50% Solution of the Polymers in THF

Tensile shear strength in N/mm² was measured on various substrates afterstorage for 7 days at room temperature (RT=ca. 20° C.) or for 4 weeks at40° C.

Example 6 5a 17b Wood/wood 4.01 3.92 2.72 7 days, RT Wood/PVC 1.02 0.411.96 7 days, RT Wood/alu 1.77 4.52 1.35 7 days, RT Wood/alu 3.41 1.953.49 4 weeks, 40° C.

What is claimed is:
 1. A polymer obtained by reaction of: (A) at leastone fatty acid or fatty acid derivative containing at least oneconjugated carton-carbon double bond; (B) it least one componentselected from the group consisting of maleic acid, citraconic acid,itaconic acid, aconitic acid, 3,4,5,6-tetrahydrophthalic acid andderivatives thereof, wherein said polymer has a weight average molecularweight of above 5,000.
 2. The polymer of claim 1 wherein (A) and (B) arepresent in a molar ratio of 1:0.1 to 1:10.
 3. The polymer of claim 1where in addition to (A) and (B) at least one copolymerizable alkenecomponent (C) containing no electron acceptor substituents is reacted toform the polymer.
 4. The polymer of claim 3 wherein (C) is present in amolar ratio of up to 10 relative to (A).
 5. The polymer of claim 3wherein (C) is selected from the group consisting of vinyl ethers, vinylesters, α-olefins, styrene, styrene derivatives, conjugatedhydrocarbons, vinyl pyrrolidones, and mixtures thereof.
 6. The polymerof claim 1 having a weight average molecular weight above 10,000 and upto 1,700,000.
 7. The polymer of claim 1 wherein (A) is selected from thegroup consisting of ricinene fatty acid, ricinene fatty acid methylesters, isomerized isolene fatty acids, methyl esters of isomerizedisolene fatty acids, dehydrated castor oil, conjugated safflower oil,and sunflower oil.
 8. The polymer of claim 1 wherein (A) is an aliphaticunsaturated carboxylic acid containing 16 to 24 carbon atoms and two ormore conjugated carbon-carbon double bonds, an ester of said aliphaticunsaturated carboxylic acid, an amide of said aliphatic unsaturatedcarboxylic acid, or a mixture thereof.
 9. The polymer of claim 1 whereinsaid polymer is modified with one or more reagents selected from thegroup consisting of alcohols, amines, and epoxides.
 10. A polymerobtained by reaction of (A) it least one member selected from the groupconsisting of aliphatic unsaturated carboxylic acids containing 16 to 24carbon atoms and two or more conjugated carbon-carbon double bonds,esters of said aliphatic unsaturated carboxylic acids, and amides ofsaid aliphatic unsaturated carboxylic acid; (B) it least one compoundselected from the group consisting of maleic acid, citraconic acid,itaconic acid, aconitic acid. 3,4,5,6-tetrahydrophthalic acid, andanhydrides, imides, alkylimides, nitriles, amides alkylamides,arylamides, aldehydes, esters and semiesters thereof and mixturesthereof and (C) optionally, at least one copolymerizable alkenecomponent containing no electron acceptor substituents; wherein (A) and(B) are present in a molar ratio of 1:0.1 to 1:10 and said polymer has aweight average molecular weight of above 5,000.
 11. The polymer of claim10 wherein (A) and (B) are present in a molar ratio of 1:0.5 to 1:1.5.12. The polymer of claim 10 wherein 0.2 to 10 moles (C) are present permole of (A).
 13. The polymer of claim 10 wherein at least one of (C) isselected from the group consisting of vinyl ethers, vinyl esters,styrene, styrene derivatives, and vinyl pyrrolidones.
 14. The polymer ofclaim 10 wherein the weight average molecular weight is above 10,000 andup to 1,700,000.
 15. The polymer of claim 10 wherein (A) is selectedfrom the group consisting of ricinene fatty acid, ricinene fatty acidmethyl esters, isomerized isolene fatty acids, methyl esters ofisomerized isolene fatty acids, dehydrated castor oil, conjugatedsafflower oil, and sunflower oil.
 16. The polymer of claim 10 wherein atleast one of (A) is selected from the group consisting of10,12-octadecadienoic acid, 9-hydroxy-10,10-octadecadienoic acid,13-hydroxy-9,11-octadecadienoic acid,9,14-dihydroxy-10,12-octadecadienoic acid, 9,12, 14octadecatrienoicacid, 8,10,12-octadecatrienoic acid, elaeostearic acid, licanic acid,camolenic acid, parinaric acid, isanoic acid, isanolic acid, ximenynicacid, matricaria acid, lachnophyllic acid, mycomycinic acid, andmixtures thereof.
 17. The polymer of claim 10 wherein at least one of(A) is isomerized isolene fatty acid or ricinene fatty acid or a methylester thereof and at least one of (B) is maleic anhydride.
 18. Thepolymer of claim 10 in saponified form.
 19. The polymer of claim 10 inhydrogenated form.
 20. The polymer of claim 10 wherein said polymer ismodified with one or more reagents selected from the group consisting ofalcohols, amines, and epoxides.
 21. The polymer of claim 10 wherein saidpolymer is crosslinked.
 22. A process for producing the polymer of claim1 wherein a reaction mixture comprised of (A) and (B) is heated.
 23. Theprocess of claim 22 wherein said reaction mixture is diluted with asolvent.
 24. The process of claim 22 wherein the reaction mixture isadditionally comprised of a radical-forming initiator.
 25. A method ofbonding a first substrate to a second substrate using an adhesive,wherein said adhesive comprises the polymer of claim
 1. 26. A method ofbonding a first substrate to a second substrate using an adhesive,wherein said adhesive comprises the polymer of claim
 10. 27. A method ofcoating a substrate using a coating composition, wherein said coatingcomposition comprises the polymer of claim
 1. 28. A method of coating asubstrate using a coating composition, wherein said coating compositioncomprises the polymer of claim
 10. 29. A method of sealing a substrateusing a sealant, wherein the sealant comprises the polymer of claim 1.30. A method of sealing a substrate using a sealant, wherein the sealantcomprises the polymer of claim
 10. 31. A method of making a compositioncomprised of at least one emulsifier, dispersant, thickener or builder,said method comprising using the polymer of claim 1 as said emulsifier,dispersant, thickener or builder.
 32. A method of making a compositioncomprised of at least one emulsifier, dispersant, thickener or builder,said method comprising using the polymer of claim 10 in salt form ormodified with a polyethylene glycol as said emulsifier, dispersant,thickener, or builder.
 33. A method of filling a substrate using afiller, wherein said filler comprises the polymer of claim
 1. 34. Amethod of filling a substrate using a filler, wherein said fillercomprises the polymer of claim
 10. 35. The polymer of claim 1 wherein atleast one of (B) is maleic anhydride.
 36. The polymer of claim 10wherein at least one of (B) is maleic anhydride.